Stay ConnectedPlanning for, or already enjoying, your retirement? This is the show for you.
The success of your retirement hinges on how well you connect the dots between legal, tax, and financial planning. Join your hosts John Ross, JD and Devin Carroll, CFP® as they dig beneath the surface to help you gain the confidence and clarity needed to navigate your retirement journey successfully.
Copyright: © 2023
David asks for a general idea of what estate planning services typically cost, following up on the six-part podcast series.
Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms.
📍Contact Devin's team at https://carrolladvisory.co/podcast1
📍Contact John's team at https://www.rossandshoalmire.com/
If you're thinking, "I love the Big Picture Retirement podcast!" please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down to the "ratings and reviews" section, tap to rate with five stars, and select "Write a Review." Then be sure to let us know what you loved most about the episode!
Also, if you haven't done so already, follow the podcast. We add new content every week, and if you're not following, you'll likely miss out. Follow now!
Don't miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. https://www.carrolladvisory.com/pl/2148282517
Want to ask Devin or John your question? Just visit https://www.bigpictureretirement.com/ and click on the "Ask A Question" menu selection.
You've heard it a thousand times: "Wait until 70 to file for Social Security." But if that's such obvious advice, why do most retirees file earlier? In this episode, we uncover the hidden cost of waiting and the trade-offs most experts ignore. You'll learn how early withdrawals, taxes, and real-life emotions all change the math—and why the "right" answer isn't the same for everyone.
Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms.
📍Contact Devin's team at https://carrolladvisory.co/podcast1
📍Contact John's team at https://www.rossandshoalmire.com/
If you're thinking, "I love the Big Picture Retirement podcast!" please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down to the "ratings and reviews" section, tap to rate with five stars, and select "Write a Review." Then be sure to let us know what you loved most about the episode!
Also, if you haven't done so already, follow the podcast. We add new content every week, and if you're not following, you'll likely miss out. Follow now!
Don't miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. https://www.carrolladvisory.com/pl/2148282517
Want to ask Devin or John your question? Just visit https://www.bigpictureretirement.com/ and click on the "Ask A Question" menu selection.
Daryl wants a simple explanation of why Health Savings Accounts matter and what makes them such a powerful retirement planning tool.
Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms.
📍Contact Devin's team at https://carrolladvisory.co/podcast1
📍Contact John's team at https://www.rossandshoalmire.com/
If you're thinking, "I love the Big Picture Retirement podcast!" please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down to the "ratings and reviews" section, tap to rate with five stars, and select "Write a Review." Then be sure to let us know what you loved most about the episode!
Also, if you haven't done so already, follow the podcast. We add new content every week, and if you're not following, you'll likely miss out. Follow now!
Don't miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. https://www.carrolladvisory.com/pl/2148282517
Want to ask Devin or John your question? Just visit https://www.bigpictureretirement.com/ and click on the "Ask A Question" menu selection.
John asks if taking larger IRA withdrawals beyond his RMD to fund his daughter's Roth IRA makes sense as a strategy to reduce future RMDs, lower estate taxes, and pass on tax-free assets.
Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms.
📍Contact Devin's team at https://carrolladvisory.co/podcast1
📍Contact John's team at https://www.rossandshoalmire.com/
If you're thinking, "I love the Big Picture Retirement podcast!" please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down to the "ratings and reviews" section, tap to rate with five stars, and select "Write a Review." Then be sure to let us know what you loved most about the episode!
Also, if you haven't done so already, follow the podcast. We add new content every week, and if you're not following, you'll likely miss out. Follow now!
Don't miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. https://www.carrolladvisory.com/pl/2148282517
Want to ask Devin or John your question? Just visit https://www.bigpictureretirement.com/ and click on the "Ask A Question" menu selection.
Many retirees think they have a plan when what they really have is an investment pitch dressed up as planning. This episode uncovers why that illusion is dangerous, the costly mistakes it hides, and how to spot the difference between true planning and portfolio sales.
Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms.
📍Contact Devin's team at https://carrolladvisory.co/podcast1
📍Contact John's team at https://www.rossandshoalmire.com/
If you're thinking, "I love the Big Picture Retirement podcast!" please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down to the "ratings and reviews" section, tap to rate with five stars, and select "Write a Review." Then be sure to let us know what you loved most about the episode!
Also, if you haven't done so already, follow the podcast. We add new content every week, and if you're not following, you'll likely miss out. Follow now!
Don't miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. https://www.carrolladvisory.com/pl/2148282517
Want to ask Devin or John your question? Just visit https://www.bigpictureretirement.com/ and click on the "Ask A Question" menu selection.
Winning the lottery may be rare, but estate tax mistakes aren't. In this episode, we use the recent $1.8 billion Powerball jackpot to highlight how generational wealth can be eroded by estate taxes and how tools like a BDIT can help protect growth assets. We'll also show why this strategy isn't just for lottery winners, but for anyone holding assets with explosive growth potential.
Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms.
📍Contact Devin's team at https://carrolladvisory.co/podcast1
📍Contact John's team at https://www.rossandshoalmire.com/
If you're thinking, "I love the Big Picture Retirement podcast!" please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down to the "ratings and reviews" section, tap to rate with five stars, and select "Write a Review." Then be sure to let us know what you loved most about the episode!
Also, if you haven't done so already, follow the podcast. We add new content every week, and if you're not following, you'll likely miss out. Follow now!
Don't miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. https://www.carrolladvisory.com/pl/2148282517
Want to ask Devin or John your question? Just visit https://www.bigpictureretirement.com/ and click on the "Ask A Question" menu selection.
So far in 2025, early Social Security filings have jumped dramatically compared to last year. Nearly half of those filing early say they're doing so because they're worried about cuts. But will filing early really help? In this episode, we talk about what the data shows, what most people get wrong about Social Security cuts, and how to think about your filing strategy with clarity, not fear.
Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms.
📍Contact Devin's team at https://carrolladvisory.co/podcast1
📍Contact John's team at https://www.rossandshoalmire.com/
If you're thinking, "I love the Big Picture Retirement podcast!" please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down to the "ratings and reviews" section, tap to rate with five stars, and select "Write a Review." Then be sure to let us know what you loved most about the episode!
Also, if you haven't done so already, follow the podcast. We add new content every week, and if you're not following, you'll likely miss out. Follow now!
Don't miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. https://www.carrolladvisory.com/pl/2148282517
Want to ask Devin or John your question? Just visit https://www.bigpictureretirement.com/ and click on the "Ask A Question" menu selection.
When should you claim Social Security? For high-net-worth retirees, this is not a simple decision. In this episode, we explain why Social Security is not just a monthly check but a strategic part of a well-built retirement plan.
Devin begins by challenging the common belief that wealthy retirees do not need to think about Social Security. In reality, those with more assets often have more choices, and those choices make the timing decision even more important.
You will learn about the three core priorities that should guide how and when you file: protecting a surviving spouse, maximizing guaranteed income, and coordinating Social Security with the rest of your retirement plan. Devin explains how each of these goals can shape your filing strategy and why getting the timing right can support better outcomes for both income and taxes.
This episode also covers how delaying benefits can increase lifetime income for a surviving spouse, reduce tax burdens through coordinated withdrawals, and help create a stronger income floor that is not tied to the markets.
If you have flexibility in when you file, use it wisely. Social Security decisions should support your long-term goals, reflect your income needs, and fit within your overall tax and investment strategy.
Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms.
📍Contact Devin's team at https://carrolladvisory.co/podcast1
📍Contact John's team at https://www.rossandshoalmire.com/
If you're thinking, "I love the Big Picture Retirement podcast!" please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down to the "ratings and reviews" section, tap to rate with five stars, and select "Write a Review." Then be sure to let us know what you loved most about the episode!
Also, if you haven't done so already, follow the podcast. We add new content every week, and if you're not following, you'll likely miss out. Follow now!
Don't miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. https://www.carrolladvisory.com/pl/2148282517
Want to ask Devin or John your question? Just visit https://www.bigpictureretirement.com/ and click on the "Ask A Question" menu selection.
For many affluent retirees, the biggest financial fear isn't market volatility or rising taxes. It's this simple question: What happens if I'm not the one here to manage the plan? In this episode, we talk about a deeply personal concern shared by countless couples.
When one spouse manages the investment strategy, the tax planning, and the long-term vision, the other is often left trusting that everything will work out. That trust may work fine today, but what if something changes tomorrow? What if the surviving spouse is left with a complex financial plan they don't fully understand?
Devin shares his own story, including the moment he realized his wife might struggle to carry on the plan they had built together. From that fear came action; a series of steps to make sure she would not only inherit assets, but also confidence and clarity. You'll hear about the simple, practical moves you can make to protect the person you love, including how to start the conversation, what to document, and how to choose someone you both trust.
This episode is a must-listen if you've ever thought, I just want to make sure my spouse will be okay if something happens to me.
Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms.
📍Contact Devin's team at https://carrolladvisory.co/podcast1
📍Contact John's team at https://www.rossandshoalmire.com/
If you're thinking, "I love the Big Picture Retirement podcast!" please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down to the "ratings and reviews" section, tap to rate with five stars, and select "Write a Review." Then be sure to let us know what you loved most about the episode!
Also, if you haven't done so already, follow the podcast. We add new content every week, and if you're not following, you'll likely miss out. Follow now!
Don't miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. https://www.carrolladvisory.com/pl/2148282517
Want to ask Devin or John your question? Just visit https://www.bigpictureretirement.com/ and click on the "Ask A Question" menu selection.
Should everyday investors be allowed to hold private equity, venture capital, or even crypto in their 401(k)s? A new executive order suggests it might soon be possible. In this episode, we walk through the real implications of this move, especially for retirement savers who may not be equipped to handle the risks.
We start with a quick quiz that highlights a troubling truth: most 401(k)-only investors don't understand basic financial principles like compound interest, inflation, or diversification. If many people struggle with the fundamentals, what happens when we layer in high-fee, illiquid, and opaque investments?
You'll hear what's already allowed in retirement plans, why private equity firms are pushing for broader access, and what dangers exist when complexity is added to accounts that are supposed to be simple and secure. We share a personal example from our own experience with illiquid private investments and explain why adding these as standalone options could backfire for plan participants.
This episode also explores why this change might be happening now, what fiduciaries need to consider, and why protecting investors requires more than just offering new choices. It requires clear guidance, thoughtful planning, and honest conversations about financial literacy.
Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms.
📍Contact Devin's team at https://carrolladvisory.co/podcast1
📍Contact John's team at https://www.rossandshoalmire.com/
If you're thinking, "I love the Big Picture Retirement podcast!" please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down to the "ratings and reviews" section, tap to rate with five stars, and select "Write a Review." Then be sure to let us know what you loved most about the episode!
Also, if you haven't done so already, follow the podcast. We add new content every week, and if you're not following, you'll likely miss out. Follow now!
Don't miss the Big Picture Retirement Planning Cheat Sheet. We've distilled the essential brackets, thresholds, and rules of retirement into an easy-to-digest, three-page summary. https://www.carrolladvisory.com/pl/2148282517
Want to ask Devin or John your question? Just visit https://www.bigpictureretirement.com/ and click on the "Ask A Question" menu selection.
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